Sodium Bicarbonate → 3-Amino-6-(1H-indol-2-yl)phthalimide

HRID 20995Notes

Reaction equation

[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([C:13]2[N:14](C(OC(C)(C)C)=O)[C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6].Cl.CO.C(=O)([O-])O.[Na+]>CO>[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6]

Participants

Conditions

Temperature: 70 °C

Procedure

3-Amino-6-[1-(tert-butoxycarbonyl)indol-2-yl]phthalimide (21.8 mg, 0.0578 mmol) was dissolved in methanol (2.2 mL), and the solution was added with 10% hydrogen chloride-methanol solution (2.2 mL), followed by stirring at 70° C. for 1.3 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution, extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by preparative thin-layer chromatography (chloroform/acetone=6/1, chloroform/methanol=12/1) to obtain Compound 1 (14 mg, yield 87%).

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by preparative thin-layer chromatography (chloroform/acetone=6/1, chloroform/methanol=12/1)

Sources & evidence

ORD record: ord-57ba0fe19a30487ba9d4f58357e5f778
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745641B2

Reaction notes

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